2-Chlorobenzoxazole → Ethyl (4-(2-benzoxazolyl)amino-5-chloro-2-fluorophenyl)acetate

HRID 1372668

반응식

HRID 1372668 반응식
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[NH2:11][C:12]1[C:17]([Cl:18])=[CH:16][C:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:14]([F:25])[CH:13]=1>C1(C)C(C)=CC=CC=1>[O:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH:11][C:12]1[C:17]([Cl:18])=[CH:16][C:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:14]([F:25])[CH:13]=1

참가 물질

4

반응물 2

HCID 119862-ChlorobenzoxazoleHCID 17858807Ethyl 4-amino-5-chloro-2-fluorophenylacetate

생성물 1

HCID 58778947Ethyl (4-(2-benzoxazolyl)amino-5-chloro-2-fluorophenyl)acetate수율 74%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

In xylene (4 ml), 2-chlorobenzoxazole (278 μl, 2.43 mmol) and ethyl (4-amino-5-chloro-2-fluorophenyl)acetate (512 mg, 2.21 mmol) were heated under reflux for 2 hours. After the reaction mixture was cooled to room temperature, the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate. The resulting solution was washed with a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (7:1, v/v) eluate fractions, ethyl (4-(2-benzoxazolyl)amino-5-chloro-2-fluorophenyl)acetate (570 mg, 74%) was obtained as a pale yellow solid.

후처리

  1. temperatureunder reflux for 2 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washThe resulting solution was washed with a saturated aqueous solution of sodium bicarbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (7:1

출처 및 근거

ORD 기록
ord-4f7bd92e4e4c47be9740591b36e80cac
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157487B2

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